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According to Andy Slater, Olsen had five separate IDs on him: two from Maryland, one from New Jersey, one from North Carolina, and one from Florida. He admitted one of the Maryland IDs was a fake, and the Florida ID had the name "Ronald Stanley Regula Jr."

Olsen, a native of New Jersey, was one of the top pro-style quarterback recruits of his class. He also received interest from school like Florida and Florida State, but decided to attend the U. His brother, current NFL player Greg Olsen, also played at the University of Miami.